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I am employed by my Mistress as her sissy slave. She has a stable of Studs that she chooses one or two each night to satisfy her. My job is to milk and satisfy those studs that she doesn't use on a particular evening. I am to keep their balls drained and keep them satisfied. Also, I clean her and her chosen studs after they are done. The studs like me and cherish me for what I do for them. Every night I give myself to the four or five of them that she isn't using, and they gangbang me. We all love how they drain their balls into me. Mistress keeps my clitty in a cage so that I don't get an erection. The only way I cum is by being fucked. I usually cum like that once or twice a day.
Recently, Mistress has decided to have me milk her Studs twice a day as the believes it gives them more staying power when they are pleasing her. She also has their meals spiked with viagra and another drug which makes them produce lots of cum.
Mistress is very wealthy. She is the heiress of an immense fortune from the old money set. She and her siblings live their lives as they wish. Some of them are business tycoons, some are just enjoying their lives of leisure. Mistress is unique in that she uses her fortune to indulge her rather perverse kinks. I am fortunate that she has found me and made me what I am today.
My childhood was pretty dismal. The only thing I had in my life was my alcoholic mother. My father had disappeared from the scenery long before I was born. I was a waif with not enough to eat since my mother spent what little money she could get her hands on, on booze. I think she was relieved when Mistress sent a man around to buy me from her. Mistress had seen me walking to school one day (I absolutely hated school), and had one of her minions investigate my background. I was only in sixth grade. It turns out that my circumstances and physique were just what she was looking for.
My physique is what caught her eye. I take after my mother. I think I should have been born a girl since everything about me except for my penis is girlish. My mother said that I was more her daughter than her son. That hurt me since everyone at school teased me about my girlish looks and manners. I had slight features, and blond hair. When I let it grow long in the summers, I could easily pass for a girl if I wanted to. And I did want to! Mother had caught me several times in her clothes. She was somewhat slutty, and her clothes were a natural turn on for me.
When Mistress bought me, she had me delivered to her estate. I think she was very pleased with her purchase. I was very naive at the time about what my role was, but she dispelled that quickly.
"You are now my new sissy slave." Were the first words that she ever spoke to me. I still didn't understand completely, but within half an hour, she had my face buried in her pussy, licking for all I was worth. After she was through with me, she called the maid in to take me away. That's the way it has always been with her. When she is through with you, you are dismissed. This first time though, she instructed the maid to have me properly "prepared" and introduced to her stable.
The maid, Giselle, took me and started explaining my role to me. I was forever grateful to her for bringing me up to speed so quickly. I found myself turned on by having eaten my Mistress's pussy until she was satisfied and was eager to learn more. Giselle explained that Mistress kept a stable of Studs for her pleasure, and I was to be used to keep them happy.
She took me into a bathroom and bathed me before dressing me in a uniform similar to hers. She spent some time doing my hair and makeup. I felt so alive. It was like I was freed into what I had always been meant to be. I remember how grateful I felt when she brought me back to my Mistress for inspection. I wanted to get on my knees and thank her. Little did I know how much time I would be spending on my knees before her in the future.
Mistress used my mouth a second time, and I was even more eager than before. I think she could tell, since afterwards, she held my head in place and stroked it. Telling me, "You're going to make a fine sissy slave for me. From now on, your name is sissy." Ever since, I bubble up with happiness whenever she calls my name -- sissy.
Giselle took me back and this time spent a little time showing me how to do my makeup. Since then, Mistress has sent me for training on hair and makeup among other things. I always do my best to learn as much as possible to please her. A few years ago, she sent me to a sissy academy sponsored by one of her kinky friends. I guess there must be a large demand for sissies for there to be an official, yet underground, academy. I think I will write a whole chapter on the sissy academy if anyone is interested. While I was there, I learned a great deal about how to please a Master or Mistress, and how to give the most pleasure possible to a cock or pussy or any part of a body. They taught me everything about how to be a proper sissy for my Mistress.
After I was made-up again, Giselle took me to a different wing of the estate. It was evening, and the wing was full of guys that she referred to as Mistress's Studs. They were all in their early twenties, and spent most of their time working out. Most of them had muscles on muscles.
She gave me to one of them and told him to break me in gently as Mistress had long term plans for me. His name was Adam, and he took me back to his room and fucked me for the first time. He was slow and gentle, but it hurt. A lot. For the first time, I was thinking that I could not go though with my new place in life. Adam fucked me three more times before the maid came to collect me in the morning.
She cleaned me up and told me how I would come to love getting fucked by all Mistress's Studs. She was right. I soon learned to love it as much as I loved having them fuck my pretty mouth until they cum in it. It fact, I am almost seventeen now, and I think I am addicted to it. I guess Mistress has chosen well.
Along the way, Mistress has modified me to suit her. She has had doctors prescribe lots of pills to keep me feminine and beautiful. I now have 36c breasts, but Mistress has told me that she is going to get me implants to make my breasts even bigger. I know her Studs will like that because they often like to titty fuck me when my other holes are in use. I like it too. I adore the feeling of them shooting their hot loads all over my face and neck. It's not quite as good as when they cum inside of me, but I still love it.
Even though I am seventeen, the pills I take have kept me from growing too much. My hips have filled out, along with my breasts. I am only 5'3", and 85lbs. I weigh practically nothing compared to her Studs. All of them are over 6". Even in my highest heels, they still tower over me. Given my smallness, I often feel like a rag doll in their hands. I am often passed around like a party treat or cum rag.
Mistress keeps her stable of Studs fully stocked. They come and go for one year terms. Sometimes two years. She has a contract with each one whereby she pays them, gives them room and board and they service her. They all get along very well with each other. Often, they use her expansive estate for sporting activities and whatever else they like. They have the run of the estate. At the end of their term, they are paid a handsome sum and are free to return to their regular lives. While they are with Mistress, they have strict rules that they follow, like they must work out to keep their bodies in peak physical condition, they are not allowed to service any other women except on the rare occasions where Mistress grants permission. I am their only other sexual outlet besides Mistress. Everyone is happy with this arrangement. I sometimes think that I am the luckiest one of the bunch.
Over the years, Mistress has gone through various phases in her kinks. Some lasted longer than others, and some stuck. Lately, Mistress has taken a liking to bondage. She has ordered me to practice yoga to keep myself limber. I should say that I am usually the object of her kinks. She doesn't experiment with her kinks on the Studs except where it makes them more able to service her. Mistress enjoys tying me up in different positions for hours. She has a professional photographer take artistic pictures of me. While I am tied up, she lets her Studs use me to their hears content. After I am untied, Mistress loves to examine the marks in my skin that the ropes leave. She is fascinated by it. Last night, I was completely immobilized with my arms and legs bent back and tied in that position. I had a heavy hood on that blocked out my hearing and sight. The only sensations I had were of the Studs cocks in and on my body. I was picked up and moved around her bedroom as directed by Mistress. I was hung upside down from the ceiling and face fucked by one of her studs while the other satisfied her. Eventually, I was placed on the bed where I felt Mistress' pussy settle over my face. I happily lapped up her Studs cum and licked her until she came too. When she was through, I felt myself being carried off back to the Studs wing. No one is allowed to release me from my bondage without Mistress permission. They must have received it as they partially untied me when they got back and fucked me silly in the recreation room. When they were through with me for the night, I was released completely, and allowed to go back to my room.
My room is in the Studs wing. It is unique in that it is befitting a sissy. It is decorated with pastels and has a full dressing area and all of the accouterments that a sissy would need to keep herself ready at all times. I use it fully, but I don't sleep there very often. I am usually in the bed of one of her Studs all night long. Sometimes, I don't get enough sleep as I am passed from room to room to drain their balls in the middle of the night. Sometimes it is a blowjob, sometimes they pin me down and fuck me before shooting their huge loads deep inside of me. If I have been requested to visit another Stud that night, and I usually am, I wait until my current Stud is asleep and then quietly slip out to see the next one. Sometimes I stop by my room to clean up a little and change my clothes. That is, if I am not in some form of bondage that makes it impossible to get changed. Lately that has often been the case.
Mistress has acquired a great deal of bondage gear. I am usually in some form of bondage lately. One of her favorites is a leather armbinder. She likes to tie it off to my clitty cage from behind and have me parade around for her. She has a large dildo installed on one of the dining room chairs. When we all take our evening meal together, she likes to watch me squirm as I sit on it.
Last week, she was in a very kinky mood. Another of her latest kinks is encasement. She likes to see me totally immobilized and encased in some contraption. I wonder where she comes up with some of her ideas. They seem straight out of a medieval torture manual. She has someone who custom fabricates all of her bondage gear and apparatus. I was summoned into her room in the morning and made to disrobe. She had a couple of her studs redress me in a tight latex outfit. She had them insert a penis gag and then a latex hood which covered my entire head except for around my mouth and two nose holes to breathe through. Then they attached what felt like leather head harness that held the penis gag in place. The penis gag had a long tube attached to it. She then had them put my arms in an armbinder behind my back. I was manhandled around, and felt myself bent over the bed. One of the Studs unzipped the crotch of my outfit, and inserted a large butt plug. I felt it inflate and seat itself within me. Then I was laid on the floor and hogtied with what felt like lots of straps. Finally, I was again lifted up and sensed myself being placed in a box. Much later, after I was removed, I finally got to see that it was indeed a large crate, lined with foam padding, and a cutout in it to secure me in place. I heard and felt the pounding of the nails as the crate was sealed above me.
I don't know how she designed it, but I felt the butt plug expanding and deflating from time to time. Suddenly, I felt a shock from it. It scared me and made me jump and moan. The padding in the crate was very snug and kept me from squirming much. I felt the crate being lifted and moved as I was jostled about inside of it. I lost track of time, and I couldn't tell how long I was in there, but it felt like many hours. Sometimes the crate was upside down, sometimes sideways. The butt plug was driving me crazy, and my clitty was straining in its cage. Suddenly, I felt a very strong jolt from the butt plug, and my clitty expelled its sissy cum. Mistress had the tube from the penis gag connected to the end of my clitty cage. It took a while for my sissy cum to travel the length of the tube, but when I tasted it, I knew that it was mine (Mistress has ordered that I eat every drop of sissy cum that I expel). When my bladders was full enough that I could hold it no longer, it went through the tube and I drank it.
Finally, I sensed the crate being opened. Hands poked and prodded me to make sure that I was alive and awake. I felt tugs on my penis gag as someone unhooked the tube and hooked another one in its place. First I tasted water which I happily drank down (little did I know that Mistress has ordered the water spiked with something that would make my clitty get hard). Next I recognized the bitter taste of urine. After that, it was followed shortly with the unmistakable taste of cum. It filled me with a perverse sense of pleasure.
I felt several pairs of hands on my body, and then I felt someone remove my clitty cage. The effects of whatever Mistress had ordered put in the water had not taken effect yet, but the stimulation made my clitty stiff nonetheless. I was stroked until I was ready to cum, and then I felt the butt plug jolt me again. I came harder than I could ever remember. Someone stroked me until I had nothing left to shoot. My clitty shrunk back to its normal tiny size. I felt the clitty cage being reattached, but somehow this time it was different. It was tighter and curved differently. I could tell from the tugging that they had reattached the tube from my penis gag to my clitty cage again.
Once again, I was placed in the crate and I sensed the top being put back on and heard and felt the nails. More jostling and moving, but this time it seemed a bit rougher. The drug started taking effect, and my clitty strained against the cage. Someone must have adjusted the controls higher because the butt plug inflated further and more often. Also, the shocks were strong and more often. I came a number of times followed by my sissy urine to wash it down with.
Again, I sensed the top of the crate being removed, and this time I was lifted out of it and set on a table of some sort. Hands moved over me and disconnected most of the tubes and wires, and the butt plug was removed. I always feel empty afterwards. When the hood was removed, I saw that I was back in Mistress's bedroom, and She and several of her Studs were present. My bindings were removed and I shakily knelt on the floor before her as I have been conditioned to.
"We missed you while you were gone sissy." She started, "My Studs need their balls drained."
I saw the beautiful smile on her face and fell in love with her a million times more. "I hope you liked your trip. From now on, whenever I send you out anywhere, that is how you will be traveling. This time I sent you to be fitted for a new clitty cage. I hope you like it."
I looked down and noticed my new cage. It was silver with lots of beautiful engraving on it. It was also much tighter. It was also the most beautiful one she had ever given me.
She ordered the Studs to take me back to their wing so that I could get some rest and clean up a bit. One of them threw me over his shoulder, and they took me back. They needed their balls drained first (of course!), and they draped me over an ottoman in the dayroom and used me over and over again to release their two days worth of pent up cum. Each of them used me multiple times, and several of them couldn't wait and jerked off onto my pretty face while they were waiting their turn at one of my holes. I was exhausted when they were through, but elated at the thought of being so needed.
I stumbled back to my room and soaked in the tub for a long time. I slept in my own bed that night. I fell asleep quickly from the exhaustion with the knowledge that tomorrow I would still need to make up for time missed from keeping Mistress and her Studs happy. A number of times during the night, I felt my bed shift as one or another of her Studs dropped by to use me. They just rolled me onto my stomach and filled me from behind. They rode me until they came and quietly slipped out, letting me rest.
Throughout most of Mistress's uses of me, I am usually impeccably dressed and made up to please her. I have a dress similar to a Maids uniform, but it is much tighter and pushes my breasts up into an appealing cleavage. Underneath, Mistress has me wear a tight corset. That is one of her phases that seems to have stuck. She likes me wearing corsets (and so do I), and has had me fitted for several of various patterns. She had ordered me to undergo waist training. The corsets work out nicely as they all have garters to hold up my stocking which Mistress prefers over pantyhose. Over the years, the heels I wear have gotten higher and higher to the point where I can't walk normally in flats. Shoes are the one area where Mistress has allowed me to choose for myself. I did my best to choose whatever I thought pleased her the most. Usually, it is what is considered fuck-me-pumps. Often can be heard the clicking of my high heels as I am bent over and fucked from behind with one of her Studs fucking up into me, lifting me off of the ground. The sound of my heals fills the air along with my screams and moans.
Mistress has my dressing room filled with whatever strikes her fancy. When I notice something new, I wear it immediately to please her. Her taste in my wardrobe has gone through phases. She likes to experiment with different styles. Usually, her tastes has been lots of lace and tight fitting outfits. Lots of pencil skirts, often of leather. She also attires me in lots of silk and satin. Lately, the colors she has chosen are mostly darks, with a lot of black corsets. She enjoys dressing me up in a femme-fatale style, and then putting me in heave bondage for her Studs to ravage for hours on end.
Her Studs can use me anytime, anywhere, except when Mistress is using me. I am conditioned to display eagerness and pleasant enthusiasm, although my eagerness and enthusiasm are genuine. They usually take advantage of this policy to their hearts content. Sometimes they have me kneel between their legs and blow them as they relax in the day room or in the sauna, or anywhere else that they may be when they find themselves in the mood to use me. When kneeling and servicing one of her Studs, often I feel a hard cock press into me from behind then while they guy talk above me. I don't mind one bit. One one hand, they treat me as a utensil, and on the other hand, the treat me as a loving cherished member. I do my best to treat them in whatever manner pleases Mistress.
Sometimes, I am called out to their sports games to service them during breaks. With the bondage gear that Mistress has been using on me lately, I am usually carried out and often laid across a convenient surface and fucked silly. One time, they stuck a funnel in my mouth and circle jerked off into it. I think they were competing to see who could cum the most. I was in bliss the whole time.
Oh yes, my caged clitty. Mistress decided to put my clitty in a cage several years ago. I am sometimes allowed out of it, but it is usually on me all the time. In fact, it feels odd to have it removed for too long. Mistress said that it was to keep my from pleasing myself so that I would keep my focus on pleasing her and her Studs. She has had several different ones custom made for me over the years. Some are plastic, some are metal. Some are shaped and curved differently. Usually, she has them colored in pastels that she said are befitting a sissy. I like the ones that don't present a big bulge in my panties. All of them have some sort of ring to attach a leash so Mistress can control me, and all of them are locked on with Mistress keeping the only key.
Here are a couple of more examples from my life. Mistress went though a period of objectification. That is, she enjoyed turning me into objects. Almost always, I was secured to a metal frame that held me in whatever position was desired, like a table, lamp, chair, etc. She would then have me placed around her mansion. I was secured in a way in which my holes were available for use, and her studs would use me like that. I think being made a coffee table was the most popular. For several hours, I was placed in the recreation room and the studs would just walk up and use me for their release and then go back to whatever they were doing.
When Mistress sends me back to the sissy academy for training from time to time, she always packs me away in a box for shipment. Her last few times have gotten more elaborate. She had added earphones to hypnotically train me during transit, and has added suction devices to my breasts. By the time I am removed from the box, I am a babbling orgasm on heels.
Mistress has finally sent me for surgery to enlarge my breasts. She had me elaborately packed and shipped to one of the premier surgeons in Brazil. I had never been shipped so far, so she sent along one of her studs who traveled first class while I was in a box in the hold of her private jet. Although Mistress has the wealth to ship me by whatever means she wishes, she usually ships me domestically via a common currier. The whole event took five days, and the whole time I was yearning to get back to my Mistress and her studs. I was addicted to their cum. Luckily, the stud that was with me fed me several times a day, and even filled a condom full of cum while I was in surgery.
When I awoke from surgery with my new 38D breasts, I was amazed. They felt so full and heavy. They were very sore at first, but it diminished rapidly within a day or two. I loved my new breasts so much. I couldn't wait to get back to Mistress to profess my love and gratitude for her. Her stud was able to enjoy fucking them on my last night there before I was packed and shipped back. He oiled them up and fucked my tits twice. We both enjoyed the way he painted me pretty face with his huge loads of cum. After he came the second time, my thoughts turned to how much Mistress' other studs were going to enjoy fucking them, and how much pent up cum would await me when I got back. Mmmmm.
When I got back, Giselle immediately took me to get cleaned up and dressed. Mistress wanted to see how well I turned out. Mistress had my entire wardrobe replaced with new clothes to fit my new figure. I was presented to Mistress in a severe underbust corset that highlighted my new breasts. Mistress was very pleased, and I was allowed to show my gratitude for the next few hours. Mistress sat on my face and let me make love to her pussy with my mouth for a long time. She played with my breasts the whole time, pinching and massaging them and generally mauling them to her hearts content. Several times, she draped herself over my body while one of studs mounted her from behind and fucked her. After they came, Mistress would upright herself and feed me while going back to playing with my new breasts. When she had had enough, her studs carried me off to the recreation room to empty their weeks worth of cum in me and on me several times over. I was one happy sissy slave by the time they were through. I slept in my own bed that night with them coming in to maul my new breasts and fuck me several times throughout the night.
Occasionally, Mistress likes to invite a few of her kinky friends over with their sissy slaves. She likes to humiliate me as much as possible for their entertainment. She knows that I love it since I have been conditioned to please her, and will suffer any humiliation to please her. At one of her gatherings, she had me heavily bound and placed on a table. In my mouth was a gag fitted with a funnel. Her guests were allowed to put anything they wanted to in it. I tasted lots of cum, wine, and even urine. My stomach was bloated by the end of the night. She was especially pleased with me that night, and my clitty cage was remove, and I was allowed to cum in a condom while one of her studs fucked me from behind for the viewing pleasure of her guests. Of course I had to suck the condom clean afterwards. I loved her all the more afterwards. Another time, she had me collect the used condoms from her male guests after they were through cumming in them and collect the cum. I drank it down while they watched. I even licked the wine glass that I drank it from.
What can I say. I am very happy being my Mistress' sissy slut. I wouldn't trade places with anyone for all the rice in china. If there is anything that anyone would like to know more about, let me know.
sissy